Copper‐Catalyzed C−H Difluoroalkylation of Coumarins with Fluoroalkyl Bromides
Min Rao, Zhenwei Wei, Yaofeng Yuan, Jiajia Cheng
Abstract
Abstract An efficient method for the copper‐catalyzed selective C−H difluoroalkylation of coumarins and with low cost and readily available ethyl bromodifluoroacetate and N ‐phenyl bromodifluoroacetamide has been reported. This reaction exhibits good functional group tolerance with respect to coumarins and difluoroalkylation reagents, and several redox‐sensitive substrates have been successfully C−H difluoroalkylated in good to high yield. This design could further expand the scope to other heteroarenes, including furan, benzofuran, pyrrole, pyridinone, chromenone, indole, and quinolinone. A mechanism involving copper‐catalyzed in‐situ generation of fluoroalkyl radical is proposed.
Topics & Concepts
BenzofuranChemistryReagentCatalysisCopperFuranIndole testYield (engineering)PyrroleFunctional groupRedoxCombinatorial chemistryOrganic chemistryMedicinal chemistryMaterials sciencePolymerMetallurgyFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsRadical Photochemical Reactions